Intramolecular anodic olefin coupling reactions: Use of the reaction rate to control substrate/product selectivity

Angewandte Chemie - International Edition

Volumn 49, Issue 43, 2010, Pages 8004-8007

  Xu, Hai Chao ^a   Moeller, Kevin D ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

Amino acids; Cyclization; Dithioketene acetals; Electrochemistry; Oxidation potential

Indexed keywords

CARBON ATOMS; COUPLING REACTION; DITHIOKETENE ACETALS; OXIDATION POTENTIAL; OXIDATION POTENTIALS; PIPECOLIC ACID;

AMINO ACIDS; ANODIC OXIDATION; ELECTROCHEMISTRY; FUNCTIONAL GROUPS; OLEFINS; REACTION RATES;

CYCLIZATION;

ACETAL DERIVATIVE; ALKENE; AMINE; AMINO ACID;

ARTICLE; CHEMISTRY; CYCLIZATION; DRUG CONTRAINDICATION; ELECTROCHEMISTRY; ELECTRODE; SYNTHESIS;

ACETALS; ALKENES; AMINES; AMINO ACIDS; CYCLIZATION; ELECTROCHEMISTRY; ELECTRODES;

EID: 78349290412     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201003924     Document Type: Article

References (49)

1. For a review, see:, K. D. Moeller, Synlett 2009, 1208 - 1218.
2. H.-C. Xu, K. D. Moeller, J. Am. Chem. Soc. 2008, 130, 13542 - 13543
3. H.-C. Xu, K. D. Moeller, J. Am. Chem. Soc. 2010, 132, 2839 - 2844.
4. H.-C. Xu, K. D. Moeller, Org. Lett. 2010, 12, 1720 - 1723.
5. For reviews of cyclic amino acid derivatives, see
6. K.-H. Park, M. J. Kurth, Tetrahedron 2002, 58, 8629 - 8659
7. C. Cativiela, M. D. Diaz-de-Villegas, Tetrahedron: Asymmetry 2000, 11, 645.
8. For recent references, see
9. S. Mitsunaga, T. Ohbayashi, S. Sugiyama, T. Saitou, M. Tadokoro, T. Satoh, Tetrahedron: Asymmetry 2009, 20, 1697 - 1708
10. Y.-G. Wang, H. Mii, T. Kano, K. Maruoka, Bioorg. Med. Chem. Lett. 2009, 19, 3795 - 3797
11. M. Kaname, M. Yamada, S. Yoshifuji, H. Sashida, Chem. Pharm. Bull. 2009, 57, 49 - 54
12. J. S. Dickstein, M. W. Fennie, A. L. Norman, B. J. Paulose, M. C. Kozlowski, J. Am. Chem. Soc. 2008, 130, 15794 - 15795
13. V. F. V. Prazeres, L. Castedo, C. González-Bello, Eur. J. Org. Chem. 2008, 3991 - 4003
14. S. T. M. Simila, S. F. Martin, Tetrahedron Lett. 2008, 49, 4501 - 4504
15. K. Undheim, Amino Acids 2008, 34, 357 - 402, and references therein.
16. For leading references concerning the use of lactam-based peptidomimetics containing cyclic amino acid derivatives, see
17. J. Cluzeau, W. D. Lubell, Biopolymers 2005, 80, 98 - 150
18. L. Halab, F. Gosselin, W. D. Lubell, Biopolymers 2000, 55, 101 - 122
19. S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789 - 12854; for additional lead references, see
20. F. Polyak, W. D. Lubell, J. Org. Chem. 1998, 63, 5937 - 5949
21. T. P. Curran, L. A. Marcaurell, K. M. OSullivan, Org. Lett. 1999, 1, 1225 - 1228
22. F. Gosselin, W. D. Lubell, J. Org. Chem. 2000, 65, 2163 - 2171
23. F. Polyak, W. D. Lubell, J. Org. Chem. 2001, 66, 1171 - 1180
24. Z. Feng, W. D. Lubell, J. Org. Chem. 2001, 66, 1181 - 1185.
25. For synthetic routes to peptidomimetics containing cyclic amino acid derivatives, see
26. W. L. Scott, J. Alsina, J. H. Kennedy, M. J. ODonnell, Org. Lett. 2004, 6, 1629 - 1632
27. C. Palomo, J. M. Aizpurua, A. Benito, J. I. Miranda, R. M. Fratila, C. Matute, M. Domercq, F. Gago, S. Martin-Santamaria, A. Linden, J. Am. Chem. Soc. 2003, 125, 16243 - 16260
28. L. Colombo, M. Di Giacomo, V. Vinci, M. Colombo, L. Manzoni, C. Scolastico, Tetrahedron 2003, 59, 4501 - 4513
29. K. Dolbeare, G. F. Pontoriero, S. K. Gupta, R. K. Mishra, R. L. Johnson, J. Med. Chem. 2003, 46, 727 - 733
30. E. M. Khalil, A. Pradhan, W. H. Ojala, W. B. Gleason, R. K. Mishra, R. L. Johnson, J. Med. Chem. 1999, 42, 2977 - 2987
31. J. Aube, Adv. Amino Acid Mimetics Peptidomimetics 1997, 1, 193 - 232
32. Y. Tong, J. Olczak, J. Zabrocki, M. C. Gershengorn, G. R. Marshall, K. D. Moeller, Tetrahedron 2000, 56, 9791 - 9800
33. S. Duan, K. D. Moeller, Tetrahedron 2001, 57, 6407 - 6415
34. B. Liu, J. D. Brandt, K. D. Moeller, Tetrahedron 2003, 59, 8515 - 8523.
35. For examples of the use of electrochemistry to functionalize cyclic amino acids, see
36. L. M. Beal, B. Liu, W. Chu, K. D. Moeller, Tetrahedron 2000, 56, 10113 - 10125
37. J. C. Simpson, C. Ho, E. F. B. Shands, M. C. Gershengorn, G. R. Marshall, K. D. Moeller, Bioorg. Med. Chem. 2002, 10, 291 - 302, and references therein.
38. J. D. Brandt, K. D. Moeller, Heterocycles 2006, 67, 621 - 628.
39. H.-C. Xu, J. D. Brandt, K. D. Moeller, Tetrahedron Lett. 2008, 49, 3868 - 3871.
40. P. G. M. Wuts, T. W. Greene, Protective Groups in Organic Synthesis, 4 th ed., Wiley, New York, 2007, pp. 855 - 859.
41. -1.
42. For other examples, see
43. K. D. Moeller, L. V. Tinao, J. Am. Chem. Soc. 1992, 114, 1033 - 1041
44. S. H. K. Reddy, K. Chiba, Y. Sun, K. D. Moeller, Tetrahedron 2001, 57, 5183 - 5197
45. Y. Huang, K. D. Moeller, Tetrahedron 2006, 62, 6536 - 6550.
46. For experimental details, please see the Supporting Information.
47. B. Liu, S. Duan, A. C. Sutterer, K. D. Moeller, J. Am. Chem. Soc. 2002, 124, 10101 - 10111.
48. J. D. Brandt, K. D. Moeller, Org. Lett. 2005, 7, 3553 - 3556.
49. The radical cation generated from the oxidation can undergo a very rapid intramolecular electron-transfer reaction. Hence, it does not matter which of the two functional groups undergoes oxidization first. See, for example:, S. Duan, K. D. Moeller, J. Am. Chem. Soc. 2002, 124, 9368 - 9369.